Silane coupling agents having ambifunctionality are known in the art to provide a stable bond between two dissimilar substrates, usually organic to inorganic, such as organic polymers to inorganic substrates, e.g., glass, mineral fillers, metals, and metallic oxides. The bond between the inorganic and organic components generally results in greater strength and service life to the polymer.
Polymerizable silane coupling agents are commercially available from numerous sources. Despite their general availability, however, only nonfluorinated hydrocarbon materials are known. The polymerizable group contains either (meth)acrylate, allyl, styryl, amino, or epoxy functionalities, while the silane group is usually an alkoxy silyl moiety (generally methoxy or ethoxy) which serves as a binding site to hydroxy-functional inorganic substrates via displacement of the alkoxy groups. Additional information concerning silane coupling agents may be found in the book by E. P. Pleuddeman ("Silane Coupling Agents", Plenum Press: New York, 1982, p 20-23 and 97), as well as in technical reports by S. Sterman and J. G. Marsden entitled "Theory of Mechanisms of Silane Coupling Agents in Glass Reinforced and Filled Thermoplastic and Thermosetting Resin Systems", Union Carbide Corporation, New York, and "A Guide to Dow Corning Silane Coupling Agents", Dow Corning Corporation, 1985, pp 2-13.
Substitution of fluorine for hydrogen in polymers and coatings is often desirable to impart useful properties such as lower surface energy. Typically, incorporation of fluorine into polymers and coatings has been made by copolymerizing (meth)acrylate monomers derived from (meth)acrylic acid and highly fluorinated alcohols. However, (meth)acrylates often polymerize at slow rates and provide polymers which possess inadequate thermal and hydrolytic stabilities.
Fluorinated (meth)acrylamide monomers have been described in several patents. U.S. Pat. Nos. 2,743,297 and 3,997,604 disclose fluorinated (meth)acrylamide monomers prepared by the reaction of fluorinated secondary or primary amines and (meth)acryloyl chloride. A complication in the synthesis is the removal of by-product hydrogen chloride.
2-Alkenyl azlactones are known to react with certain nucleophiles such as primary amines and alcohols to afford (meth)acrylamide-functional products. It has been disclosed in U.S. Pat. No. 4,931,582 that linear fluorinated-alcohols and -diols when reacted with 2-alkenyl azlactones yield desirable fluorinated acrylamide monomers.
It is believed that the reaction of a hydroxy-functional fluorinated acrylamide and an isocyanatoalkylsilane to afford fluorinated acrylamide silane monomers of the invention has not been previously reported.